A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters

被引：12

作者：

Murauski, Kathleen J. R. ^{[1
]}

Walden, Daniel M. ^{[2
]}

Cheong, Paul Ha-Yeon ^{[2
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, 2145 Sheridan Rd, Evanston, IL 60208 USA

[2] Oregon State Univ, Dept Chem, 153 Gilbert Hall, Corvallis, OR USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 21期

关键词：

N-heterocyclic carbene; NHC; ternary catalysis; lactone; cooperative catalysis; Umpolung; homoenolate; N-HETEROCYCLIC CARBENE; HYDROGEN-BOND DONORS; CONJUGATE UMPOLUNG; GAMMA-BUTYROLACTONES; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CARBON ACTIVATION; TERTIARY-AMINES; DUAL CATALYSIS;

D O I：

10.1002/adsc.201701015

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A general and enantioselective N-heterocyclic carbene (NHC)-catalyzed lactonization of simple enals and alpha-ketoesters has been discovered using a new ternary cooperative catalytic system. The highly selective annulation was achieved by using a combination of a chiral NHC, a hydrogen-bond donor, and a metal salt, facilitating self-assembly of the reactive partners. A proposed model for this new mode of NHC chiral relay catalysis is supported by experimental and computational mechanistic studies.

引用

页码：3713 / 3719

页数：7

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